S-tert-Butyl-D-cysteine hydrochloride
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S-tert-Butyl-D-cysteine hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-003569
CAS number
200353-65-7
Molecular Formula
C7H15NO2S·HCl
Molecular Weight
213.70
S-tert-Butyl-D-cysteine hydrochloride
IUPAC Name
(2S)-2-amino-3-tert-butylsulfanylpropanoic acid;hydrochloride
Synonyms
D-Cys(tBu)-OH HCl; (S)-2-Amino-3-(Tert-Butylthio)Propanoic Acid Hydrochloride
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Melting Point
208-212 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C7H15NO2S.ClH/c1-7(2,3)11-4-5(8)6(9)10;/h5H,4,8H2,1-3H3,(H,9,10);1H/t5-;/m1./s1
InChI Key
MHBMYFJKEBCMDR-NUBCRITNSA-N
Canonical SMILES
CC(C)(C)SCC(C(=O)O)N.Cl

S-tert-Butyl-D-cysteine hydrochloride, a chiral cysteine derivative widely employed in bioscience research, boasts a multitude of applications. Here are four key applications:

Chiral Synthesis: A cornerstone in chiral synthesis, S-tert-Butyl-D-cysteine hydrochloride serves as a fundamental building block for generating enantiomerically pure compounds. Its significance in the pharmaceutical realm is paramount, given that enantiopurity can profoundly impact the efficacy and safety of drugs. The compound’s chirality facilitates the synthesis of intricate molecules with exceptional specificity, revolutionizing the creation of pharmaceutical entities with unparalleled precision.

Peptide Synthesis: In the realm of peptide synthesis, this compound plays a pivotal role as a protecting group for cysteine residues, mitigating undesired side reactions during the peptide formation process. Following the synthesis of the desired peptide chain, the selective removal of the tert-butyl group yields functional cysteine. This intricate process underscores the compound’s crucial contribution to the synthesis of complex peptides with unparalleled precision and purity.

Proteomics Research: Within the realm of proteomics, S-tert-Butyl-D-cysteine hydrochloride aids researchers in probing protein structure and function. By enabling the modification of cysteine residues, researchers can delve into protein folding and stability, illuminating key aspects of protein dynamics. This application stands as a cornerstone for unraveling the intricacies of protein behavior and paves the way for designing cutting-edge protein-based therapeutics with unprecedented efficacy and precision.

Drug Development: At the forefront of drug discovery and development, S-tert-Butyl-D-cysteine hydrochloride serves as a pivotal starting material for synthesizing cysteine-containing analogs. These analogs act as potential leads in crafting innovative pharmaceuticals with desirable biological activities, driving the creation of novel therapeutics targeting diverse diseases. This innovative approach underscores the compound’s pivotal role in advancing drug development and underscores its potential in shaping the future landscape of pharmaceutical interventions.

1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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